Hydrogen Peroxide → 2,3-Dihydro-2,3,3-trimethyl-1H-inden-1-one

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Reaction Steps

KH (32 g at 35% in mineral oil, 280 mmol, 1.4 equiv.) was suspended in THF (160 ml) and 3,3-dimethyl-1-indanone (as prepared as described above, 32 g, 200 mmol) in THF (150 mmol) was added. The green suspension was stirred for 1.5 h at RT, then triethylborane (1M solution in THF, 280 ml, 280 mmol, 1.4 equiv.) was added slowly. After 1 h stirring at RT methyl iodide (40 g, 280 mmol, 1.4 equiv.) was added and the suspension stirred for 48 h at RT. Treatment with H2O (240 ml), 10% aq. NaOH (240 ml) and 30% aq. H2O2-solution (240 ml) under occasional cooling was followed by extraction with MTBE. The organic layer was washed with brine, dried over MgSO4 and concentrated in a rotary evaporator. Bulb-to-bulb distillation (0.05 mbar/100° C.) yielded 24.8 g (71%) of product.

Provenance & Evidence